Remarkable stereospecific conjugate additions to the Hsp90 inhibitor celastrol

Journal of the American Chemical Society

Volumn 133, Issue 49, 2011, Pages 19634-19637

  Klaić, Lada ^a   Trippier, Paul C ^a   Mishra, Rama K ^a   Morimoto, Richard I ^a   Silverman, Richard B ^a  

^a NORTHWESTERN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION PRODUCTS; BIOLOGICAL PROBES; CONJUGATE ADDITION; FACIAL SELECTIVITY; GAIN INSIGHT; MICHAEL ADDITIONS; MODE OF ACTION; NATURAL PRODUCTS; NMR SPECTROMETRY; NUCLEAR OVERHAUSER EFFECTS; ORBITAL INTERACTION; PHARMACOPHORES; PROTEIN TARGETS; STEREOSPECIFIC; STEREOSPECIFIC MANNER; STEREOSPECIFICITY;

NUCLEAR MAGNETIC RESONANCE; NUCLEOPHILES; SULFUR;

DENSITY FUNCTIONAL THEORY;

CELASTROL; NUCLEOPHILE;

ARTICLE; DRUG SELECTIVITY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEAR OVERHAUSER EFFECT; PHARMACOPHORE; PROTEIN TARGETING; STEREOSPECIFICITY;

HSP90 HEAT-SHOCK PROTEINS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; QUANTUM THEORY; STEREOISOMERISM; TRIPTERYGIUM; TRITERPENES;

EID: 83055161400     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja208359a     Document Type: Article

References (38)

1. Trott, A.; West, J. D.; Klaic, L.; Westerheide, S. D.; Silverman, R. B.; Morimoto, R. I.; Morano, K. A. Mol. Biol. Cell 2008, 19, 1104
2. Westerheide, S. D.; Bosman, J. D.; Mbadugha, B. N.; Kawahara, T. L.; Matsumoto, G.; Kim, S.; Gu, W.; Devlin, J. P.; Silverman, R. B.; Morimoto, R. I. J. Biol. Chem. 2004, 279, 56053
3. Cleren, C.; Calingasan, N. Y.; Chen, J.; Beal, M. F. J. Neurochem. 2005, 94, 995
4. Mu, T. W.; Ong, D. S.; Wang, Y. J.; Balch, W. E.; Yates, J. R., III; Segatori, L.; Kelly, J. W. Cell 2008, 134, 769
5. Kiaei, M.; Kipiani, K.; Petri, S.; Chen, J.; Calingasan, N. Y.; Beal, M. F. Neurodegener. Dis. 2005, 2, 246
6. Wang, J.; Gines, S.; MacDonald, M. E.; Gusella, J. F. BMC Neurosci. 2005, 6, 1
7. Zhang, Y. Q.; Sarge, K. D. J. Mol. Med. 2007, 85, 1421
8. Huang, F. C.; Chan, W. K.; Moriarty, K. J.; Zhang, D. C.; Chang, M. N.; He, W.; Yu, K. T.; Zilberstein, A. Bioorg. Med. Chem. Lett. 1998, 8, 1883
9. Allison, A. C.; Cacabelos, R.; Lombardi, V. R.; Alvarez, X. A.; Vigo, C. Prog. Neuropsychopharmacol. Biol. Psychiatry 2001, 25, 1341
10. Ngassapa, O.; Soejarto, D. D.; Pezzuto, J. M.; Farnsworth, N. R. J. Nat. Prod. 1994, 57, 1
11. Chang, F. R.; Hayashi, K.; Chen, I. H.; Liaw, C. C.; Bastow, K. F.; Nakanishi, Y.; Nozaki, H.; Cragg, G. M.; Wu, Y. C.; Lee, K. H. J. Nat. Prod. 2003, 66, 1416
12. Abbas, S.; Bhoumik, A.; Dahl, R.; Vasile, S.; Krajewski, S.; Cosford, N. D.; Ronai, Z. A. Clin. Cancer Res. 2007, 13, 6769
13. Hieronymus, H.; Lamb, J.; Ross, K. N.; Peng, X. P.; Clement, C.; Rodina, A.; Nieto, M.; Du, J.; Stegmaier, K.; Raj, S. M.; Maloney, K. N.; Clardy, J.; Hahn, W. C.; Chiosis, G.; Golub, T. R. Cancer Cell 2006, 10, 321
14. Kamal, A.; Boehm, M. F.; Burrows, F. J. Trends Mol. Med. 2004, 10, 283
15. Solit, D. B.; Chiosis, G. Drug Discov. Today 2008, 13, 38
16. Trepel, J.; Mollapour, M.; Giaccone, G.; Neckers, L. Nat. Rev. Cancer 2010, 10, 537
17. Whitesell, L.; Mimnaugh, E. G.; De Costa, B.; Myers, C. E.; Neckers, L. M. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 8324
18. Schulte, T. W.; Akinaga, S.; Soga, S.; Sullivan, W.; Stensgard, B.; Toft, D.; Neckers, L. M. Cell Stress Chaperones 1998, 3, 100
19. Whitesell, L.; Lindquist, S. L. Nat. Rev. Cancer 2005, 5, 761
20. Sharp, S.; Workman, P. Adv. Cancer Res. 2006, 95, 323
21. Zhang, T.; Hamza, A.; Cao, X.; Wang, B.; Yu, S.; Zhan, C. G.; Sun, D. Mol. Cancer Ther. 2008, 7, 162
22. Sreeramulu, S.; Gande, S. L.; Gobel, M.; Schwalbe, H. Angew. Chem., Int. Ed. 2009, 48, 5853
23. Yang, H.; Chen, D.; Cui, Q. C.; Yuan, X.; Dou, Q. P. Cancer Res. 2006, 66, 4758
24. Zhang, T.; Li, Y.; Yu, Y.; Zou, P.; Jiang, Y.; Sun, D. J. Biol. Chem. 2009, 284, 35381
25. Chadli, A.; Felts, S. J.; Wang, Q.; Sullivan, W. P.; Botuyan, M. V.; Fauq, A.; Ramirez-Alvarado, M.; Mer, G. J. Biol. Chem. 2010, 285, 4224
26. Gunatilaka, A. A. Triterpenoid Quinonemethides and Related Compounds (Celastroloids); Springer: Vienna/New York, 1996; Vol. 67.
27. Zhou, Q. Natural Diterpene and Triterpene Quinone Methides: Strucutres, Synthesis, and Biological Potentials; John Wiley & Sons: Hoboken, NJ, 2009; Vol. 1.
28. Rose, I. A.; Hanson, K. R.; Wilkinson, K. D.; Wimmer, M. J. Proc. Natl. Acad. Sci. U.S.A. 1980, 77, 2439
29. Gunatilaka, A. A. W.; Wimalasiri, W. R. J. Chem. Res. 1992, 30
30. Nakanishi, K.; Takahashi, Y.; Budzikiewicz, H. J. Org. Chem. 1965, 30, 1729
31. Clark, J. H.; Miller, J. M.; So, K.-H. J. Chem. Soc., Perkin Trans. 1 1978, 941
32. Jaguar, version 7.8; Schrödinger, LLC: New York, 2011.
33. Mineva, T. THEOCHEM 2006, 762, 79
34. Mineva, T.; Parvanov, V.; Petrov, I.; Neshev, N.; Russo, N. J. Phys. Chem. A 2001, 105, 1959
35. Contreras, P. R.; Fuentealba, P.; Galvan, M.; Perez, O. Chem. Phys. Lett. 1999, 304, 405
36. Chamorro, E.; Perez, P. J. Chem. Phys. 2005, 123, 114107
37. Pearson, R. G. J. Am. Chem. Soc. 1963, 85, 3533
38. Silverman, R. B. The Organic Chemistry of Enzyme-Catalyzed Reactions; Academic Press: San Diego, 2002; Chap. 3.